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MedKoo Cat#: 577825 | Name: Benafentrine free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Benafentrine, also known as AH 21-132, is a PDE4 inhibitor. AH 21-132 has bronchodilator activity in anaesthetised, ventilated guinea-pigs when administered intraduodenally, intravenously or by inhalation. Inhaled AH 21-132 also provides bronchodilatation in healthy human volunteers in whom bronchoconstriction has been induced by inhaled methacholine.

Chemical Structure

Benafentrine free base
Benafentrine free base
CAS#35135-01-4 (free base)

Theoretical Analysis

MedKoo Cat#: 577825

Name: Benafentrine free base

CAS#: 35135-01-4 (free base)

Chemical Formula: C23H27N3O3

Exact Mass: 393.2052

Molecular Weight: 393.49

Elemental Analysis: C, 70.21; H, 6.92; N, 10.68; O, 12.20

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
76166-55-7 (dimaleate) 35135-01-4 (free base)
Synonym
Benafentrine; AH 21-132; AH-21-132 AH21-132; AH 21132; AH-21132 AH21132;
IUPAC/Chemical Name
N-(4-((4aR,10bS)-8,9-dimethoxy-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridin-6-yl)phenyl)acetamide
InChi Key
DCDXHGMCXGHXBM-WOJBJXKFSA-N
InChi Code
InChI=1S/C23H27N3O3/c1-14(27)24-16-7-5-15(6-8-16)23-18-12-22(29-4)21(28-3)11-17(18)19-13-26(2)10-9-20(19)25-23/h5-8,11-12,19-20H,9-10,13H2,1-4H3,(H,24,27)/t19-,20-/m1/s1
SMILES Code
CC(NC1=CC=C(C2=N[C@]3([H])CCN(C)C[C@]3([H])C4=CC(OC)=C(OC)C=C24)C=C1)=O.O=C(O)/C=C\C(O)=O.O=C(O)/C=C\C(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 393.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Yoshimura T, Kurita C, Nagao T, Usami E, Nakao T, Watanabe S, Kobayashi J, Yamazaki F, Tanaka H, Nagai H. Effects of cAMP-phosphodiesterase isozyme inhibitor on cytokine production by lipopolysaccharide-stimulated human peripheral blood mononuclear cells. Gen Pharmacol. 1997 Oct;29(4):633-8. doi: 10.1016/s0306-3623(96)00580-0. PMID: 9352314. 2: Dietrich C, Kilbinger H. 5-HT1A receptor-mediated inhibition of acetylcholine release from guinea pig myenteric plexus: potential mechanisms. Neuropharmacology. 1996 Apr;35(4):483-8. doi: 10.1016/0028-3908(95)00197-2. PMID: 8793911. 3: Seldon PM, Barnes PJ, Meja K, Giembycz MA. Suppression of lipopolysaccharide- induced tumor necrosis factor-alpha generation from human peripheral blood monocytes by inhibitors of phosphodiesterase 4: interaction with stimulants of adenylyl cyclase. Mol Pharmacol. 1995 Oct;48(4):747-57. PMID: 7476903. 4: Abrahamsen J, Nedergaard OA. Role of cyclic AMP in stimulation-evoked release of 3H-noradrenaline from rabbit isolated ear artery. Pharmacol Toxicol. 1995 Mar;76(3):185-9. doi: 10.1111/j.1600-0773.1995.tb00127.x. PMID: 7617543. 5: Nagai H, Takeda H, Iwama T, Yamaguchi S, Mori H. Studies on anti-allergic action of AH 21-132, a novel isozyme-selective phosphodiesterase inhibitor in airways. Jpn J Pharmacol. 1995 Feb;67(2):149-56. doi: 10.1254/jjp.67.149. PMID: 7542355. 6: Nagai H, Yamaguchi S, Kitagaki K, Tsuruoka N, Koda A. Priming with murine recombinant interleukin-5 resulted in the augmentation of PAF-induced airway hyperresponsiveness to histamine in guinea pigs. Life Sci. 1993;52(17):PL147-51. doi: 10.1016/0024-3205(93)90070-j. PMID: 8464339. 7: Foster RW, Rakshi K, Carpenter JR, Small RC. Trials of the bronchodilator activity of the isoenzyme-selective phosphodiesterase inhibitor AH 21-132 in healthy volunteers during a methacholine challenge test. Br J Clin Pharmacol. 1992 Dec;34(6):527-34. doi: 10.1111/j.1365-2125.1992.tb05658.x. PMID: 1493085; PMCID: PMC1381455. 8: Souness JE, Carter CM, Diocee BK, Hassall GA, Wood LJ, Turner NC. Characterization of guinea-pig eosinophil phosphodiesterase activity. Assessment of its involvement in regulating superoxide generation. Biochem Pharmacol. 1991 Jul 25;42(4):937-45. doi: 10.1016/0006-2952(91)90056-b. PMID: 1651083. 9: Giembycz MA, Barnes PJ. Selective inhibition of a high affinity type IV cyclic AMP phosphodiesterase in bovine trachealis by AH 21-132. Relevance to the spasmolytic and anti-spasmogenic actions of AH 21-132 in the intact tissue. Biochem Pharmacol. 1991 Jul 15;42(3):663-77. doi: 10.1016/0006-2952(91)90330-8. PMID: 1650218. 10: Suganuma T, Imai T, Idaira K, Konno S, Hoshino H, Okazawa A, Adachi M, Takahashi T, Maeda M, Tsuji A. [The effect of AH 21-132 on airway hyperresponsiveness induced by ozone exposure]. Arerugi. 1991 May;40(5):529-37. Japanese. PMID: 1883268. 11: Small RC, Berry JL, Boyle JP, Chapman ID, Elliott KR, Foster RW, Watt AJ. Biochemical and electrical aspects of the tracheal relaxant action of AH 21-132. Eur J Pharmacol. 1991 Jan 17;192(3):417-26. doi: 10.1016/0014-2999(91)90234-h. PMID: 1647318. 12: Small RC, Foster RW, Berry JL, Chapman ID, Elliott KR. The bronchodilator action of AH 21-132. Agents Actions Suppl. 1991;34:3-26. PMID: 1665308. 13: Elliott KR, Berry JL, Bate AJ, Foster RW, Small RC. The isoenzyme selectivity of AH 21-132 as an inhibitor of cyclic nucleotide phosphodiesterase activity. J Enzyme Inhib. 1991;4(3):245-51. doi: 10.3109/14756369109035848. PMID: 1645399. 14: Sanjar S, Aoki S, Kristersson A, Smith D, Morley J. Antigen challenge induces pulmonary airway eosinophil accumulation and airway hyperreactivity in sensitized guinea-pigs: the effect of anti-asthma drugs. Br J Pharmacol. 1990 Apr;99(4):679-86. doi: 10.1111/j.1476-5381.1990.tb12989.x. PMID: 2361168; PMCID: PMC1917560. 15: Sanjar S, Aoki S, Boubekeur K, Chapman ID, Smith D, Kings MA, Morley J. Eosinophil accumulation in pulmonary airways of guinea-pigs induced by exposure to an aerosol of platelet-activating factor: effect of anti-asthma drugs. Br J Pharmacol. 1990 Feb;99(2):267-72. doi: 10.1111/j.1476-5381.1990.tb14692.x. PMID: 2328394; PMCID: PMC1917376. 16: Kings MA, Chapman I, Kristersson A, Sanjar S, Morley J. Human recombinant lymphokines and cytokines induce pulmonary eosinophilia in the guinea pig which is inhibited by ketotifen and AH 21-132. Int Arch Allergy Appl Immunol. 1990;91(4):354-61. doi: 10.1159/000235141. PMID: 2210871. 17: Small RC, Boyle JP, Elliott KR, Foster RW, Watt AJ. Inhibitory effects of AH 21-132 in guinea-pig isolated ileum and taenia caeci. Br J Pharmacol. 1989 Aug;97(4):1174-81. doi: 10.1111/j.1476-5381.1989.tb12576.x. PMID: 2551443; PMCID: PMC1854628. 18: Small RC, Boyle JP, Duty S, Elliott KR, Foster RW, Watt AJ. Analysis of the relaxant effects of AH 21-132 in guinea-pig isolated trachealis. Br J Pharmacol. 1989 Aug;97(4):1165-73. doi: 10.1111/j.1476-5381.1989.tb12575.x. PMID: 2551442; PMCID: PMC1854606. 19: Racké K, Schwörer H, Kilbinger H. Adrenergic modulation of the release of 5-hydroxytryptamine from the vascularly perfused ileum of the guinea-pig. Br J Pharmacol. 1988 Nov;95(3):923-31. doi: 10.1111/j.1476-5381.1988.tb11722.x. PMID: 2463031; PMCID: PMC1854204. 20: Briggs CA, McAfee DA, McCaman RE. Long-term regulation of synaptic acetylcholine release and nicotinic transmission: the role of cyclic AMP. Br J Pharmacol. 1988 Feb;93(2):399-411. doi: 10.1111/j.1476-5381.1988.tb11447.x. PMID: 2833971; PMCID: PMC1853801.